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Trimethylsilylation and methylation of 1-hydroxybenzotriazole 3-oxide

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Abstract

Trimethylsilylation and methylation of 1 -hydroxybenzotriazole 3-oxide (1) proceed regioselectively and afford 1-trimethylsilyloxy- and 1-methoxybenzotriazole 3-oxides, respectively. The first compound easily undergoes fast hydrolysis and methanolysis, but does not react with nitroethane at 20 °C. A fast reversible 1,5-O,O-migration of the SiMe3 group is observed for this compound.

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References

  1. E. T. Apasov, A. M. Churakov, Yu. A. Strelenko, S. L. Ioffe, B. A. Dzhetigenov, and V. A. Tartakovsky,Tetrahedron, 1995,51, 6775.

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  2. E. T. Apasov, B. A. Dzhetigenov, Yu. A. Strelenko, A. V. Kalinin, and V. A. Tartakovsky,Izv. Akad. Nauk SSSR, Sci. Khim., 1991, 1394 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 1234 (Engl. Transl.)].

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation

    S. L. Ioffe, A. E. Fedorov, Yu. A. Strelenko, A. M. Churakov & V. A. Tartakovsky

Authors
  1. S. L. Ioffe
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  2. A. E. Fedorov
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  3. Yu. A. Strelenko
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  4. A. M. Churakov
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  5. V. A. Tartakovsky
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Additional information

The authors thank V. I. Gulevskaya for DTA analysis of compound4.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2283–2285, November, 1995.

The present work was supported by the Russian Foundation for Basic Research (project No. 93-03-18461).

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Ioffe, S.L., Fedorov, A.E., Strelenko, Y.A. et al. Trimethylsilylation and methylation of 1-hydroxybenzotriazole 3-oxide. Russ Chem Bull 44, 2190–2192 (1995). https://doi.org/10.1007/BF00696731

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  • DOI: https://doi.org/10.1007/BF00696731

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